


Tom Holland's Embarrassing and Sometimes Erotic Journey to Becoming Spiderman

by Freethewillies



Category: Spider-Man (Tom Holland Movies), tom holland - Fandom
Genre: Embarrassment, F/M, Gay, Homoeroticism, Humiliation, M/M, Mutual Masturbation, Naked Male Clothed Female, Naked Male Clothed Male, Premature Ejaculation, Small Penis, jacking off together
Language: English
Status: In-Progress
Published: 2020-12-22
Updated: 2020-12-23
Packaged: 2021-03-10 21:01:39
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 4,122
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28243593
Author URL: https://archiveofourown.org/users/Freethewillies/pseuds/Freethewillies
Relationships: Tom Holland/Original Character(s)
Kudos: 15





	1. In Which An Explosive Secret Comes Out During an Interview

“In here Tom,” the attending said, opening the door to a small room which stemmed from the narrow hallway, “you’re interview will be in twenty miuntes so just relax a bit.”

“Thank you, sir,” Emily responded for him. Tom just silently gulped and entered the small room, his mind was rapt with other thoughts to acknowledge even the movement of his own two feet. Luckily his manager Emily was used to dealing with Tom’s nerves and knew precisely how to guide him in these situations.

The man shut the door to give the pair some privacy and Tom sunk into the lumpy beige sofa tucked into the corner of the room. There was little else to be found here besides the sofa: a mirror, a pair of chairs, and a tall leafy plant to give just the space a perfunctory level of warmth.

“Don’t be nervous time, you’ve done thousands of interviews. This one will be as easy as all the rest.” Emily set her bag on one of the chairs and sat on the other.

“You know that’s not why I’m nervous, Ms. Emily.” She didn’t respond, because of course she knew what he was referring to. Tom was up for the role of Spiderman, and the decision was to be made any day now. All the work he had done could very shortly have been for naught; the auditions alone were grueling but the work out regimen to get his body superhero ready was damn near barbaric. The transformation was radical, and he still often found himself catching glimpses of his own body when taking a shower or changing and feeling like he was watching someone else. But it’d all be worth it if he got the role. To get such a lucrative part at just nineteen, he’d be set for life.

“Well if you are nervous, you know that means we’re going to have to curtail your little problem,” she said after a pause. Tom blushed bright red and refused to look at her. “The last thing you want is to be worrying about that today.”

She was right of course. He could already feel the building tension and surely the added stress of the interview would tip him over the edge. Little problem was what Emily called it to be polite, but it didn’t make it any less embarrassing.

Like anybody, Tom experienced somatic symptoms with heightened anxiety: sweaty palms, churning stomach, dizziness. However, when the feeling grew particularly large, Tom would be affected in a rather peculiar way. A flurry of sensation would overcome genitals, as if a thousand hands were grasping at his cock but just barely missing. Every brush of fabric sent shivers of anxious pleasure down his shaft and into his balls which yearned for release. The feeling would build until it became unbearable and release was the only option. Release of course meaning filling his loom with the fruits of his seed.

“I have some magazines if you like?” she started rummaging through her bag.

“That really won’t be necessary,” Tom said, even redder than before. He stood up, only to have to use his hands to cover the tenting in his pants. He scurried to their adjacent bathroom before Emily could properly offer the lube she had freshly pulled from the bag.

“Hurry up though, we’re on in five!” she shouted through the door as he hastened to unbuckle his trousers. He didn’t need reminding. Nothing would be worse than getting halfway and then going out to do the interview. The buckle jingling happily as he pulled down his pants and briefs in one motion so that they rested on the floor around his ankle.

He saw himself in the mirror, his erect pale cock sticking upright, the top tucked under the bottom of his flannel shirt. He turned around to look at his ass, the thing most transformed by his recent foray into extreme fitness. He squeezed his right cheek slightly to confirm just how plump it had become and glimpsed a hint of butthole. He had been toying with trying to finger himself lately, but of course now was not the time to try new things. Now was the time for efficiency.

He waddled over to the toilet and sat down. He stared unblinkingly at the erect penis which curved slightly back so that pointed at him. Was he really ready to be Spiderman? Here he was about to jack off in this dimly lit bathroom so that he wouldn’t cum himself later. And look at his cock? Was that really Spiderman’s cock? Only five inches and a relatively narrow five inches at that. Sure he had pretty remarkably sized balls, but that only served two purposes: making his flaccid cock look smaller and creating ridiculous amounts of cum to release during this interview if he didn’t get to stroking.

“Two minutes!” Emily’s voice called.

“Oh shit,” he grasped his cock and quickly started pumping his foreskin up and down his shaft. He watched the swollen head of his penis poke in and out of its cover willing the cum to fly out. 

“One minute!”

Oh man, oh shit, oh man! He needed sexy things to think about, but he was lacking real experiences to pull from. That time that girl bent at the gym and her tits fell out. That was hot wasn’t it? What if they had fallen on your face? And then she groped you and said ‘Oh Tom your dick is huge and totally could be Spiderman’s dick…oh shit the Spiderman thing!

“It’s time to go Tom they’re here!”

Fuck Fuck Fuck! Something else. My ass was hot. I’d fuck an ass like that. Wait does that make me gay? Or conceited? Fuck

“Tom!”

He had to go. He shoved his angry horny dick back in his briefs and rebuckled his belt. He just had to keep it in for a bit, no problem. He opened the door.

“We’ve got to go man,” the attending said. Tom shuffled his crotch and shot a worried look at Emily to hint that the deed was not complete. But there was nothing to be done. He followed the man and soon he was sitting across from a man with thick rimmed glasses and thin rimmed hair. His cock was pressed firmly in the cotton of his briefs.

“Thank you for coming, Tom”

“Well I haven’t yet-I mean thank you for having me.” He had never been more aware of his genitals. His balls were squashed firmly against the seat and his cock was testing the limits of the button on his pants.

“I’m especially excited to talk to you because I hear you might be the next Spiderman? Is that true?”

“Oh really?” Tom said with a voice much higher than his own. Please talk about anything but Spiderman. The feeling was building and becoming irresistible. He clenched the armrest until it hurt.

“Yes, it’d be quite the role if you get it.”

It felt like his cock was a family of butterflies trying to flee in every direction at once. He could feel the semen loaded for launch, with tiny bits escaping the dilating tip of his penis.

“Yeah, it would really – uh really,” it was happening, his cock had pulled the trigger and all that was left was the little willpower Tom could exert to delay the inevitable by a few seconds. He stood up a bit and squatted on his seat, a trick Emily had devised to cover moments like these.

The cum burst from his cock, socking the cotton and dribbling down all sides of his dick. Each firing of his cock was accompanied with a recoil which unloaded full streams of semen all over his crotch. 

“It would really feel good to get the role,” Tom said clenching his teeth and muscles as his dick continued to twitch and fire.

“Anyone you’d like to see play Mary Jane?

“You know, there’s lots of great actresses out there.” The cum was already cold and clammy by the time the last twitches finished. He angles his body back to avoid it dumping into the rest of his underwear, but it just sent it down either side of his balls, between his thighs. A single dribble of semen trickled over his left nut.

“And of course we can’t forget that you’re here promoting a movie now.”  
Every part of his crotch was damp and gooey. It had even traveled now so his taint was squat firmly in the gooey mess, and a bit stuck between the earliest hints of buttcheeks.

He sat in his mess for the remainder of his interview, trying to move as little as possible as every shift leaked the semen to a new part of his bare underside. Finally, the interview ended. He shook the bespeckled man’s hand and waddled hurriedly back to his dressing room with Emily close behind. The cum had fully saturated his underwear so that now some was trickling down his left leg.

Emily threw a fresh pair of tighty whities at him from her bag, and he was so eager to change he just pulled everything off right then.

“Do you have a towel?” He asked ashamedly, his cum covered flaccid cock was shriveled back neatly into its foreskin and dangling meekly between his legs. She obliged and he wiped everything from his body.

Just then, the attending burst into the room. “Mr. Holland, they’ve announced that you’re going to be Spider…oh sorry!” he was out of the room as quick as he was in it, but he had delivered the news Tom wanted to hear. 

He was Spiderman. And his little spidercock was already perky again.


	2. In Which Tom Has Some Embarrassing Measurements

**Summary for the Chapter:**

> In this chapter, Tom gets fitted for his Spiderman costume, but that could be more revealing than he initially thought.

“It’s so exciting, isn’t it?” Emily said as they climbed the stairs. Tom was a few steps behind her; though only a few inches taller, her pace was incredible. “It’s all happening so fast.”

“It sure is,” Tom agreed, though he wasn’t sure if he was talking about the process of becoming Spiderman, or climbing the stairs. Why was the costume department at Marvel Studios so high up? And why did they take the stairs? His newly muscled bum was already difficult to fit in his old pants, after this the seams might start splitting. Finally the pair reached the appropriate floor and entered the hallway where a young blond man with a clipboard and a headset greeted them.

“Hello Tom! And Ms. Emily too! My name is Dustin and I’m going to be Tom’s errand guy while he works for Marvel! Anything you need, I’m here for” He extended a hand with a bright toothy smile and an energy Tom couldn’t help but be taken in by. About a half foot taller than Tom and equally skinny throughout his body, Tom got the overall impression of an over eager beanpole.

“Nice to meet you Dustin,” Tom said grasping his hand.

“And Ms. Emily, you are needed on the next floor up to finalize the some of the finer parts of the deal I’m told.”

“Of course, good luck Tom.” And she disappeared the way they came.

“So today Mrs. Tanaka will be doing the fitting and measurements for your costume ok?” Tom nodded. “Follow me then!” He was once again half a step behind, this time because Dustin’s stride was fairly longer than his. They reached the double doors labeled “Costume Department” and walked through.

On the other side was an almost indescribable hayfever of fashion, people, and movement. The whole room was the size of a Wearhouse, and workers darted and weaved between rows of dresses and outfits and any other thing you could put on your body. And with Dustin’s gesture, he and Tom became part of the darting and weaving until finally they reached a long table near the center. Standing behind it was a short Japanese woman with long straight black hair. She was dressed much more modestly that Tom had expected: a sleek black shirt and tight black capris. She spoke without even looking up from the embroidery work she was currently doing on a scarf

“Mr. Holland, you are here for your measurements, two minutes early, exactly how I like it.” Dustin smiled as this must’ve been his planning. Then again, Tom didn’t know if he had seen him not smiling yet. “Clothes off please”

“Um ok.” Tom said hastened to comply. This woman seemed like business and he didn’t want to waste her time. He pulled his shirt over his head, revealing his lean muscular torso. He noticed a few workers around him stop to look and blushed a bit.

“Can you hold this for me, yeah?” Tom said, hand his shirt to Dustin.

“Sure!” Dustin said, and Tom swore he saw Dustin give him the quickest glance at his body which made Tom blush even more. He tried to ignore it and pulled off his pants and handed those to Dustin as well who was now politely looking at the ceiling.

But the rest of the room didn’t seem to share Dustin’s tact, and Tom quickly felt the eyes of a dozen curious seamstresses on his tighty whitey clad body. All except Mrs. Tanaka, who without looking up elaborated “ All of your clothes Mr. Holland, this will be a very form fitting suit. Measurements must be precise.”

She wanted him to get naked? Here in front of all these people? Luckily he had jacked off before coming in or the embarrassment of it all might have given him a boner. But that also meant that his dangling little cock was as small as it ever was. But what choice did he have.

He gave his bulge two little squeezes to try to pump a little blood in before pulling his waistband down. The back of his briefs resisted the oversized hump of his ass before snapping down with the front. He handed his briefs to Dustin who continued his professional staring contest with the ceiling.

Tom closed his eyes for a second, trying to forget that he was buck naked in a room full of onlookers. Onlookers, he realized, had probably seen every dick in the Avengers. And somehow he doubted his 2 inch dangler compared favorably to Thor’s might hammer.

“Sheila, Sheldon, get to measuring, “ Mrs. Tanaka said, and when Tom opened his eyes, two young Asian designers, one guy and one girl, had descended upon him with measuring tapes and protractors. Tom assumed they must be Mrs. Tanaka’s children as both shared her angular features and focused stares. The girl had her mom’s straight black hair but augmented it with a flower in her ear which she occasionally pulled out to chew on as she thought about what to measure next. Sheldon on the other hand had hair which could only be described as poodle-like, and he stayed back with a large notepad, scribbling and sketching as Sheila stated measurements joylessly.

They started from the top, bending his arms and measuring his chest as necessary. She wrapped the measure around his broad chest, tickling him slightly as she traversed his armpits. She giggled along with him, which her mother seemed to disapprove of.

When she reached his navel, she had him turn around. Every aspect of the curve of his buttocks was noted, even going as far as to measure the widgth and length of his taint, a process which caused her to graze the back of his balls frequently. “You have very little hair,” she noted, “that will be good for the chaffing.”

“Uh thanks,” Tom said, as she spun him around again. She was on her knees, and therefore his cock was now inches from her face. 

“That’s not a compliment, just an observation,” she said, as she measure the length of his feet.

“Oh yeah, sorry, not sure why I said thanks.” She stared pulling the tape measure from his foot alo.ng the inside of his leg and up his thigh. He bit his lip, not sure what would happen when she reached his groin. Whatever it was, it surely had quite of large chance of causing an erection.

“I forgot you Brits don’t cut your willies,” she said. 

“Yeah, we don’t.” The measuring tape had reached the bottom of his balls and before he could offer to move them aside, Sheila had a full grasp of his manhood (admittedly not much) and held them up so that she could measure to the millimeter where his ballsack started,

Don’t get hard, don’t get hard, don’t get hard. Her cool hands fondled him gently as she finagled the measurement before releasing them. They dropped back into position with a little bounce, still flaccid. But there was still the other side to do.

“I think its quite cuter your way,” she said, finally looking up to smile at him, as she drew the tape up the other side of his inner leg. “And that was a compliment,” she added with a little laugh that Tom wasn’t sure wasn’t making fun of him.

“Uh, thanks” he responded, as she once again manhandled him. But this time, the added power of a cute girl complimenting his dick and the slight manipulation of her hand sent the blood rushing to his cock. He could feel in pressing into her palm as it grew. 

Tom looked at the ceiling, anywhere but where anyone could catch his eye. She released her grip and let his hard cock fall into place so that his dick pointed its full five inches from his body, practically on her face.

“Fuck” Tom said, “sorry”.

“Whoah,” Sheldon said, looking up from his sketch pad with such surprise that his poodle hair bounced around like jello.

“It’s…it’s ok…it happens!” Sheila said, though he could tell by her voice it must not happen often. “Hey everybody mind their own business!” she snapped. Tom refused to look anywhere but the ceiling, but that comment told him that his boner must have not gone undetected by the others in the room.

“Hey no pressure man, but it’s actually kind of important that you’re not hard for the next fitting. We have to do you’re bulge flattener.” Sheldon said. 

“Bulge flattener?” Tom said, finally looked back at the room.

“Yeah these are family movies, and we can’t have you running around in skintight lycra with your dick print on the screen” he explained, “so we give you one of these” he held up what looked like an athletic cup.

“Here, sit down” Sheila said “and we’ll just…wait for it to go down.” He sat in a chair at the table, which his dick standing 90 degrees from the floor. 

“Oh for goodness sake, give the man some privacy” Dustin said bringing over a stray piece of floral cloth he must have picked from one of the rack. He lay it on Tom’s lap, and Tom tucked his erection in his thigh to avoid the tenting. Dustin tried to give a whatareyougoingtodo smile, which   
calmed Tom down a bit.

They sat in complete silence for a few minutes before Tom sheepishly said “It’s not…it’s not a problem anymore. Sheila had him stand up and Sheldon pulled out a box of twenty of the cup like objects in a row of sizes.

“Now the idea is to get it as small as possible, so don’t be upset if it’s not one of the larger ones ok” Sheldon said. Tom nodded, but he couldn’t help but notice that the first one he pulled was the third from smallest.

Sheldon held the cup up to Tom’s crotch and pressed it against his skin. The cups themselves were transparent which served as a window to Tom’s genitalia to allow Sheldon to inspect just how much extra room there was. In this case, too much as Sheldon reached for the next smallest size.

A little bit better, but there was still room for his cock to bounce around. Tom blushed as Sheldon discreetly grabbed the smallest one and looked apologetically at Tom and said, “This’ll do then.”

“He has a small penis, give him the thong,” Mrs. Yanaka interjected.

“Mom!” Sheila and Sheldon said simultaneously.

“What!? For small penises we use the thong. He’s a grown man, he’s not offended. He knows his penis is small. He sees it everyday. You know you have a small penis?”

“Um…yeah,” Tom said sheepishly. It was hard to argue when he was very visibly failing to fill the smallest dick holder they had. Sheldon removed the cup to look for the thong, leaving the penis the room had just agreed was tiny on full display for scrutiny (which of course only caused it to cower further into retreat).

Finally Sheldon pulled out the thong and Tom pulled it on. It wasn’t like the thongs he had seen om girls, well girls on the internet. It was just a tight triangle of fabric which firmly held his bits in place, and a string which ran up the length of his buttcrack.

“See,” Mrs. Tanaka said, “Smooth as a barbie doll. There could be a vagina under there for all we know.” Tom’s entire body was red with embarrassment. This whole event had been thoroughly humiliating and he was practically running out of the room when Dustin said it was time to go meet Emily to finish the contract.

They walked along the highway with a brisk silence. How could he ever face anyone after this. That whole room of people, surely “New Spiderman has shrimp dick” will be on the cover of every tabloid next morning. Suddenyl Dustin pulled him into one of the doors. It was a small walk in closet filled with some food for catering.

“What are we doing in here,” Tom asked, temporarily forgetting the traumatic happenings from before.

“I just…That had to suck man. I’m sorry that happened to you.” Dustin said, looking at the floor. This simple act of kindness nearly replaced all the doubt Tom was having. Nearly.

“Thanks man, it really did suck.”

“I want to show you something,” he said and pulled down his pants more quickly than Tom could protest. “It’s only fair that you get to see somebody else since you had to be on display today.”  
Dustin’s plump pale cock hung an inch below his balls, and even had a few freckles to match Dustin’s face which Tom couldn’t help but find cute. And above his cock was a bright patch of red hair which looked like had a haphazard attempt at a trimming.

“You’re a fire crotch,” Tom smiled.

“Yeah I hate it,” Dustin said

“Nah man, it’s like shazam! Right there. Big and bold!” Tom found himself laughing, much sooner than he had expected to.

“Well maybe if I could get a girl to see it it’d make an impression,” Dustin laughed.

“You a virgin too?” Tom asked. He had assumed he was the only guy his age who wasn’t getting laid based on his friends tales of their exploits.

“Yeah, just lady hand to destress me. And I will need some destressing tonight.”

“You’re telling me.” The two stood there a bit, Dustin still with his dick hanging out. “You know, we’re going to be on the road together, we’ll have to get used to destressing around each other.”

“Yeah I guess so.” Dustin’s dick was growing to full mast. It was quite thick, especially at the top, and completely lacked and curve, just like his beanpole body. He grabbed it and moved his hand slowly, subtly tugging it in a way that could be taken back if he had misread the situation.

Tom’s own dick sprung out when he pulled down his pants and the pair stood side by side against the wall, furiously pumping their cocks in their hands. Tom could feel the cool of the wall against his doughy ass. He tried to stare straight ahead, but his eyes would much rather watch Dustin’s cock than the leftover ketchup packets on the shelf. He stole guilty glances at Dustin’s dick, which looked like an oversized sausage in his hands. Each glance sent a shiver of tingles down his shaft until-

“Fuck fuck fuck”, heaps of cum spurt from Tom’s dick and splashed the floor with what felt like an audible thud. Dustin wasn’t far behind, but instead of verbalizing the experience, he clutched Tom’s shoulder and squeezed with the same vigor he squeezed his semen on to the floor.

“I…feel…so much…better.” Tom panted.

Dustin just smiled that big smile Tom had seen since he first met him this morning. “We’re late for your meeting.:

**Author's Note:**

> This is my first time creating a fan fiction. Let me know what you think :)


End file.
